1,4-Dioxane → Tert-butyl 4-(5-chloro-6-methoxypyridin-3-yl)-3-methylbenzoate

HRID 529716ノート

反応式

HRID 529716 の反応式
Br[C:2]1[CH:3]=[C:4]([Cl:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:19][C:20]1[CH:21]=[C:22]([CH:30]=[CH:31][C:32]=1B1OC(C)(C)C(C)(C)O1)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].O1CCOCC1>C(OCC)(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl.[Pd+2].O>[Cl:10][C:4]1[CH:3]=[C:2]([C:32]2[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[CH:21][C:20]=2[CH3:19])[CH:7]=[N:6][C:5]=1[O:8][CH3:9]

参加物

9

反応物 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 404270045-Bromo-3-chloro-2-methoxypyridineHCID 68937270Tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

生成物 1

HCID 86682280Tert-butyl 4-(5-chloro-6-methoxypyridin-3-yl)-3-methylbenzoate収率 88.8%

試薬・触媒・溶媒 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 17952575palladium(II)dichloromethane触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a 250 mL RBF was added 5-bromo-3-chloro-2-methoxypyridine (1.5 g), tribasic potassium phosphate (2.86 g, 13.5 mmol), bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.275 g, 6.74 mmol), tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (2.27 g, 7.13 mmol), dioxane (50 mL) and water (3 mL). The flask was sealed and was stirred at 80° C. overnight. The reaction was cooled to room temperature, diluted with ethyl acetate, washed with water, filtered and concentrated. The resultant residue was purified by column chromatography to yield tert-butyl 4-(5-chloro-6-methoxypyridin-3-yl)-3-methylbenzoate (2.0 g, 5.99 mmol). MS ESI calc'd. for C18H21ClNO3 [M+H]+ 334.1, found 334.0.

後処理

  1. customThe flask was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with water
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant residue was purified by column chromatography

出典と根拠

ORDレコード
ord-15506110a8904d8d95aeca17b1be198c
出典データセット
uspto-grants-2016_05
特許番号
US09346825B2

反応ノート

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